US5936001A - Disinfecting and sterilizing concentrate containing an aromatic dialdehyde and a neutral pH buffering system - Google Patents

Disinfecting and sterilizing concentrate containing an aromatic dialdehyde and a neutral pH buffering system Download PDF

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Publication number
US5936001A
US5936001A US09/010,351 US1035198A US5936001A US 5936001 A US5936001 A US 5936001A US 1035198 A US1035198 A US 1035198A US 5936001 A US5936001 A US 5936001A
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disinfecting
present
solution
aromatic dialdehyde
concentration
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US09/010,351
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Phillip A. Block
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Ethicon Inc
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Ethicon Inc
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Priority to US09/010,351 priority Critical patent/US5936001A/en
Application filed by Ethicon Inc filed Critical Ethicon Inc
Assigned to JOHNSON & JOHNSON MEDICAL DIVISION OF ETHICON, INC. reassignment JOHNSON & JOHNSON MEDICAL DIVISION OF ETHICON, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BLOCK, PHILIP A.
Assigned to ETHICON, INC. reassignment ETHICON, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JOHNSON & JOHNSON MEDICAL DIVISION OF ETHICON, INC.
Priority to EP99300392A priority patent/EP0937395B2/en
Priority to ES99300392T priority patent/ES2200467T5/es
Priority to CA2259707A priority patent/CA2259707C/en
Priority to DE69908206T priority patent/DE69908206T3/de
Priority to JP11048716A priority patent/JP2000001406A/ja
Priority to AU13180/99A priority patent/AU747387B2/en
Priority to US09/320,598 priority patent/US6071972A/en
Publication of US5936001A publication Critical patent/US5936001A/en
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • the present invention relates to disinfecting and sterilizing solutions, and more particularly to a disinfecting and sterilizing concentrate containing an aromatic dialdehyde and a neutral pH buffering system.
  • Aromatic dialdehyde disinfecting and sterilizing solutions are well known in the art. Aromatic dialdehyde solutions have bacteriostatic and fungistatic activity. They are useful for disinfecting or sterilizing medical devices or environmental surfaces. Unfortunately, present aromatic dialdehyde solutions limit the concentration of the aromatic solution to less than or equal to 5 w/w% of the total solution because aromatic dialdehydes have limited aqueous solubility. While water-miscible solvents may increase the solubility of aromatic dialdehyde, the solvents adversely affect the buffering systems of aromatic dialdehyde disinfecting and sterilizing solutions.
  • the limit on the amount of ortho-phthalaldehyde used in the concentrate solution is a function of the solubility of the aromatic dialdehyde in water, which is about 5 w/w%.
  • Bruckner et al. indicate that the concentration may be increased above the 5 w/w% level with the addition of water-miscible solvents. They specifically state that suitable solvents include methanol, ethanol, isopropanol, glycols, tetrahydrofuran, dimethyl sulfoxide, and dioxane. But, Bruckner et al. do not discuss or address any adverse affects caused by the additional solvents. There are some adverse affects.
  • Bruckner et al. observe that an alkalinating or acidifying salt can be used in the compositions (solutions) as a buffer to maintain a desired composition pH during storage and use.
  • Bruckner specifically discloses an alkali metal carbonate or bicarbonate, e.g., sodium bicarbonate or potassium bicarbonate, or phosphate as a buffering salt.
  • the buffer may be an organic carboxylate salt such as sodium citrate, sodium acetate, potassium hydrogen phthalate, potassium citrate, or potassium acetate, or an inorganic borate salt such as potassium or sodium borate.
  • the pH range from about 6 up to about 8 is preferred to ensure materials compatibility of certain medical instruments or utensils.
  • Certain medical instruments or utensils are prepared from materials such as anodized aluminum, carbon steel, and rubber. These materials are chemically incompatible with environments outside the pH range from about 6 up to about 8. Therefore, to prevent harm to medical instruments or utensils prepared from these materials, a buffering system is required to maintain a pH in the range from about 6 up to about 8.
  • the concentration of water-miscible solvents required to increase the concentration of the aromatic dialdehyde above 5 w/w% are generally incompatible with the buffering system of the aromatic dialdehyde solutions. That is, as the concentration of the aromatic dialdehyde is increased by the addition of water-miscible solvents, the physical stability of the buffering system is diminished. This physical instability is particularly apparent with phosphate buffering systems. To achieve and maintain the desired pH range from about 6 to about 8, the concentration of the buffering system must be increased as the concentration of aromatic dialdehyde is increased. Accordingly, there is a need to increase the concentration of the aromatic dialdehyde and the concentration of the pH buffering system while maintaining the physical stability of the pH buffering system.
  • a disinfecting and sterilizing concentrate containing an aromatic dialdehyde and a neutral pH buffering system is provided. More specifically, there is provided a disinfecting and sterilizing concentrate comprising an aromatic dialdehyde present in a concentration greater than 5 w/w%, a water miscible solvent, and a pH buffering salt. Concentrations of greater than 5 w/w% are achieved while maintaining the physical stability of the pH buffering system. A method and a kit for preparing a disinfecting and sterilizing concentrate is also provided. Further, a reduction of the amount of waste materials is achieved by reducing the amount of packaging required to deliver aromatic dialdehyde disinfecting and sterilizing solutions.
  • a disinfecting and sterilizing concentrate comprising an aromatic dialdehyde present in a concentration greater than 5 w/w%, a water miscible solvent, and a pH buffering salt is provided.
  • the concentrate may additionally contain a stabilizer, water, and minor ingredients.
  • the water-miscible solvent increases the solubility of the aromatic dialdehyde.
  • the pH buffering salt maintains the pH of the "in use solution.” The stabilizer protects the pH buffering salt from the harmful effects of the water-miscible solvent.
  • aromatic dialdehydes useful in the present invention preferably have the formula: ##STR1## and are commonly called: ortho-phthalaldehyde, where X is CHO and Y and Z are H,
  • terephthalaldehyde where Z is CHO and X and Y are H.
  • the preferred aromatic dialdehyde is ortho-phthalaldehyde because of its good solubility in water and disinfecting and sterilizing activity.
  • the aromatic dialdehyde is present in an "in-use solution" concentration in an amount ranging from about 0.025 w/w% and 1 w/w%.
  • a preferred concentration ranges from about 0.05 w/w% to about 0.6 w/w%.
  • Suitable water-miscible solvents include solvents having either a hydroxy or carbonyl group (such as ethanol, methanol, 1,4-butanediol, ethylene glycol, propylene glycol, isopropanol, acetone, and polyols), dimethylsulfoxide, dioxane, and tetrahydrofuran. Solvents with lower human toxicity are preferable and include ethanol, 1,4-butanediol, and propylene glycol.
  • Suitable buffering salts for maintaining a pH range from about 6 to about 8 include boric acid/sodium borate, maleic acid/sodium maleate, monobasic phosphate/dibasic phosphate, and citric acid/sodium citrate.
  • Other buffering salts can achieve the desired pH range, but buffering salts with lower human toxicity are preferable.
  • cacodylate and sodium barbital are buffering salts that can achieve the desired pH, but these salts would not prove useful because they pose human toxicity problems.
  • the identified buffering salts are preferred in this order: (1) monobasic phosphate/dibasic phosphate, (2) citric acid/sodium citrate, (3) boric acid/sodium borate, and (4) maleic acid/sodium maleate.
  • aromatic dialdehydes are also incompatible with buffering systems having primary or secondary amines.
  • aromatic dialdehydes cross-link primary or secondary amine buffering systems and thereby reduce the concentration of both the aromatic dialdehyde and the buffering systems.
  • tris(hydroxymethyl) aminomethane and 2-amino-2-methyl-1,3-propanediol are amines that can cross-link in the presence of an aromatic dialdehyde.
  • Suitable stabilizers to protect the buffering salts against the adverse effects of the water-miscible solvents include polyols (such as glycerol and sorbitol) and propylene carbonate.
  • the physical stability of the buffering salt is defined as no formation of precipitates or phase separation of the buffered solution at 4° C. for a minimum of 2 weeks and is determined by visual inspection.
  • the chemical stability of the aromatic dialdehyde is defined as no loss of the aromatic dialdehyde in excess of 15 % of the total amount initially present at 40° C. for a minimum of sixty (60) days and is determined by high performance liquid chromatography.
  • Suitable minor ingredients include dyes, chelants e.g., ethylenediaminetetraacetic acid (EDTA), citric acid!, and builders e.g., sodium tripolyphosphate (STPP), other phosphonates!.
  • chelants e.g., ethylenediaminetetraacetic acid (EDTA), citric acid!
  • STPP sodium tripolyphosphate
  • minor ingredients is well known to those of ordinary skill in the art and does not affect the active ingredients of the solutions or solutions' performance.
  • phosphate buffering systems are more sensitive to alcohol (solvent) concentrations as compared to borate or maleate buffering systems. Because maleate buffering systems are not as sensitive to alcohol concentrations as other buffering systems, lower concentrations of stabilizers are appropriate. In fact, a stabilizer may be an unnecessary ingredient for certain concentrate formulations containing a maleate buffering systems. It should also be noted that some buffering systems are insoluble in alcohols and diols, for example, phosphate buffering systems are insoluble in alcohol.
  • a formulation of the concentrate is represented as:
  • a formulation of the concentrate is represented as:
  • a formulation of the concentrate is represented as:
  • the order of addition affects the formulation time.
  • the water-miscible solvent and the water are first mixed together.
  • the stabilizer is admixed.
  • the buffer salt is admixed.
  • the aromatic dialdehyde is admixed to the solution.
  • the minor ingredients are admixed.
  • the order of addition affects formulation time for at least two reasons. If the aromatic dialdehyde is added directly to the water, the aromatic dialdehyde becomes hydrated. As a hydrate, the aromatic dialdehyde dissolves more slowly in the water-miscible solvent. Accordingly, it is desirable to avoid hydration of the aromatic dialdehyde.
  • aromatic dialdehyde dissolves more slower in low pH solutions than it does in neutral pH solutions.
  • the aromatic dialdehyde is more likely to polymerize than it is in solutions having a neutral pH.
  • the boric acid buffering system will dissolve more quickly in the stabilizer glycerol if the glycerol is heated.
  • volatile solvents such as ethanol
  • a kit for preparing a disinfecting and sterilizing concentrate is provided.
  • the concentrated aromatic dialdehyde and the buffering system are maintained as two distinct solutions, as they are separately packaged, for example, in a single split-chamber bottle.
  • the split-chamber bottle provides for a single dosing method.
  • the second solution may be physically or chemically incompatible with the first solution. This embodiment is particularly useful with phosphate buffering systems because phosphate buffering systems are particularly sensitive to alcohol (solvent) concentrations.
  • a formulation for the kit is represented as:
  • a formulation for the kit is represented as:
  • a formulation for the kit is represented as:
  • the minor ingredients may be added to Solution 1, Solution 2, or both. Adding the minor ingredients to Solution 2 is preferable because it avoids any potential interaction between the minor ingredients and the aromatic dialdehyde of Solution 1. Also, a stabilizer is unnecessary in the alternate embodiment because the buffering system and the water-miscible solvent are not combined until just prior to use and at "in-use solution" concentrations. Moreover, Solution 1 and Solution 2 of the kit may be combined in various ratios, for example, 3:1, 2:1, 1:1, 1:2, and 1:3, respectively. The preferred ratio is 1:1.
  • formulations exemplify the more preferred embodiment and the more preferred alternate embodiment.
  • the formulations are at 24X concentrates, where X is the "in-use solution” concentration. It is understood that the following examples are provided to further illustrate the invention. They do not in anyway limit the scope of the present invention.
  • This formulation was prepared by first mixing the ethanol and water together. Next, the glycerol was added. The composition was then heated because the borate buffering system dissolves more quickly at higher temperatures. The boric acid and borax ingredients were then added. The resulting composition was then cooled to prevent evaporation of the ethanol. The ortho-phthalaldehyde was then added to the mixture. The minor ingredients including 0.5 w/w% of a 1% dye in water solution, 0.5 w/w% of 1% calcium sequestrant (EDTA) in water solution, and 0.2 w/w% of a copper sequestrant (benzotriazole) were then added.
  • An "in-use solution” of the concentrate was prepared by diluting the concentrate 24 times.
  • the "in-use solution” has a pH of 7.5.
  • the solution's pH decreases by only 0.3 units when the "in-use solution” is diluted by half with water.
  • the solution's pH decreases by only 0.3 units per mL of 0.1 N HCl added to the "in-use solution.”
  • This formulation was prepared by first adding the sodium hydroxide to the water. The resulting solution was cooled. Next, the maleic acid was added. The solution was again cooled. Next, the 1,4-butanediol was admixed. Then, the ortho-phthalaldehyde was admixed. The minor ingredients including 0.5 w/w% of a 1 % dye in water solution and 0.5 w/w% of 1 % calcium sequestrant (namely, EDTA) in water solution were finally added.
  • maleate buffering system did not require a stabilizer against the water-miscible solvent, 1,4-butanediol.
  • Maleate buffering systems are not particularly sensitive to solvent concentration up to 24X concentrates. If concentrates of 30X or greater are desired, a stabilizer is preferably added to protect the physical stability of the maleate buffering system.
  • An "in-use solution” of the concentrate was prepared by diluting the concentrate 24 times.
  • the "in-use solution” has a pH of 7.2.
  • the solution's pH decreases by only 0.1 units when the "in-use solution” is diluted by half with water.
  • the solution's pH decreases by only 0.05 units per mL of 0.1 N HCl added to the "in-use solution.”
  • a kit is exemplified by the following formulation.
  • a single split-chamber bottle is used.
  • the concentrated aromatic dialdehyde solution is in Chamber No. 1, and the buffering system is in Chamber No.
  • Solution 1 of this formulation was prepared by adding the ethanol to the distilled water. Next, the ortho-phthalaldehyde was added to ethanol/water mixture.
  • Solution 2 was prepared by first heating the distilled water because the phosphate salt dissolves more quickly in heated water than it does in cool water. The sodium monobasic phosphate and sodium dibasic phosphate ingredients were then added to the heated water. The minor ingredients were then added. The minor ingredients included 0.5 w/w% of a 1% dye in water solution and 0.5 w/w% of 1% calcium sequestrant (EDTA) in water solution.
  • EDTA calcium sequestrant
  • the kit of Example 3 showed physical and chemical stability at 40° C. for a minimum of thirty (30) days. After 30 days, the kit did show the formation of a precipitate or phase separation nor a loss of the aromatic dialdehyde in excess of 15% of the total amount initially present The kit was not tested beyond thirty days. The kit is expected to have continued physical and chemical stability beyond sixty (60) days because the solvent and buffering systems are maintained in separate solutions.

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US09/010,351 1998-01-21 1998-01-21 Disinfecting and sterilizing concentrate containing an aromatic dialdehyde and a neutral pH buffering system Expired - Lifetime US5936001A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US09/010,351 US5936001A (en) 1998-01-21 1998-01-21 Disinfecting and sterilizing concentrate containing an aromatic dialdehyde and a neutral pH buffering system
JP11048716A JP2000001406A (ja) 1998-01-21 1999-01-20 芳香族ジアルデヒドと中性ｐＨ緩衝システムを含む消毒及び殺菌濃縮液
EP99300392A EP0937395B2 (en) 1998-01-21 1999-01-20 Disinfecting and sterilizing concentrate containing an aromatic dialdehyde and a neutral ph buffering system
DE69908206T DE69908206T3 (de) 1998-01-21 1999-01-20 Desinfizierendes und sterilisierendes Konzentrat, welches einen aromatischen Dialdehyd und ein neutrales pH Puffersystem enthält
ES99300392T ES2200467T5 (es) 1998-01-21 1999-01-20 Concentrado desinfectante y esterilizante que contiene un dialdehido aromatico y un sistema de tamponamiento de ph neutro.
CA2259707A CA2259707C (en) 1998-01-21 1999-01-20 Disinfecting and sterilizing concentrate containing an aromatic dialdehyde and a neutral ph buffering system
AU13180/99A AU747387B2 (en) 1998-01-21 1999-01-21 Disinfecting and sterilizing concentrate containing an aromatic dialdehyde and a neutral pH buffering system
US09/320,598 US6071972A (en) 1998-01-21 1999-05-26 Disinfecting and sterilizing concentrate containing and aromatic dialdehyde and a neutral pH buffering system

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040071592A1 (en) * 2002-10-10 2004-04-15 Ioana Annis Fast dissolving solid ortho-phthalic aldehyde formulations
US6891069B1 (en) 2004-01-30 2005-05-10 Ethicon, Inc. Synthesis of 4-substituted phthalaldehyde
US20050136118A1 (en) * 2003-12-19 2005-06-23 Wu Su-Syin S. Distribution and preparation of germicidal compositions
US20050136086A1 (en) * 2003-12-19 2005-06-23 Rafael Herruzo Efficacy enhancers for germicides
US20050171121A1 (en) * 2004-01-30 2005-08-04 Zhu Peter C. Germicidal compositions containing phenylmalonaldehyde-type compounds, or mixtures of phenylmalonaldehyde-type compounds and phthalaldehydes, and methods of using such compositions for disinfection or sterilization
US20050171216A1 (en) * 2004-01-30 2005-08-04 Zhu Peter C. Germicidal compositions containing phthalaldehyde mixtures and methods of using such compositions for disinfection or sterilization
US20050171215A1 (en) * 2004-01-30 2005-08-04 Ethicon, Inc. Germicidal compositions containing halogenated phthalaldehyes, and methods of using such compositions for disinfection or sterilization
US20050238732A1 (en) * 2003-12-19 2005-10-27 Kaitao Lu Carbonated germicide with pressure control
US20070004808A1 (en) * 2005-06-29 2007-01-04 Zhu Peter C Forming germicidal aromatic dialdehydes with acetals
WO2007078163A1 (en) * 2006-01-05 2007-07-12 Lg Chem, Ltd. Stable composition of aromatic dialdehyde and method for stabilizing aromatic dialdehyde
US7476767B2 (en) 2004-01-30 2009-01-13 Ethicon, Inc. Alpha-hydroxy sulfonate aldehydes, germicidal compositions containing the alpha-hydroxy sulfonate aldehydes, or mixtures of alpha-hydroxy sulfonate aldehydes and phthalaldehydes, and methods of using the compounds or compositions for disinfection or sterilization
US20110009493A1 (en) * 2008-02-12 2011-01-13 Larry Kent Hall Broad Spectrum Disinfecting and Sterilizing Composition

Families Citing this family (5)

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Publication number Priority date Publication date Assignee Title
EP3106032A1 (en) * 2007-03-28 2016-12-21 Whiteley Corporation Pty Ltd Sterilizing composition
US20090111895A1 (en) * 2007-10-31 2009-04-30 Ethicon, Inc. Enhanced dialdehyde disinfectant and sterilization formulations
US8933008B2 (en) * 2010-04-27 2015-01-13 Whiteley Corporation Pty. Ltd. Disinfectant solution comprising synergistic, non-equilibrium aldehyde biocides
WO2012142665A1 (en) * 2011-04-19 2012-10-26 Saboori Farshid Pigment dispersions
WO2024252024A1 (en) * 2023-06-09 2024-12-12 Sartorius Bia Separations D.O.O. A method of enhanced separation of full adeno-associated virus (aav) capsids

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US4847304A (en) * 1987-05-21 1989-07-11 Surgikos, Inc. Disinfecting and sterilizing composition
US4851449A (en) * 1987-05-21 1989-07-25 Surgikos, Inc. Odorless aromatic dialdehyde disinfecting and sterilizing composition
US4971999A (en) * 1987-05-21 1990-11-20 Johnson & Johnson Medical, Inc. Odorless aromatic dialdehyde disinfecting and sterilizing composition and method of using the same
US5128051A (en) * 1991-09-30 1992-07-07 Union Carbide Chemicals & Plastics Technology Corporation Method for the control of biofouling

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US5158778A (en) † 1991-10-16 1992-10-27 Ecolab Inc. Stable antimicrobial dialdehyde composition and methods of use
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US4847304A (en) * 1987-05-21 1989-07-11 Surgikos, Inc. Disinfecting and sterilizing composition
US4851449A (en) * 1987-05-21 1989-07-25 Surgikos, Inc. Odorless aromatic dialdehyde disinfecting and sterilizing composition
US4971999A (en) * 1987-05-21 1990-11-20 Johnson & Johnson Medical, Inc. Odorless aromatic dialdehyde disinfecting and sterilizing composition and method of using the same
US5128051A (en) * 1991-09-30 1992-07-07 Union Carbide Chemicals & Plastics Technology Corporation Method for the control of biofouling

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040071592A1 (en) * 2002-10-10 2004-04-15 Ioana Annis Fast dissolving solid ortho-phthalic aldehyde formulations
US20050238732A1 (en) * 2003-12-19 2005-10-27 Kaitao Lu Carbonated germicide with pressure control
US20050136118A1 (en) * 2003-12-19 2005-06-23 Wu Su-Syin S. Distribution and preparation of germicidal compositions
US20050136086A1 (en) * 2003-12-19 2005-06-23 Rafael Herruzo Efficacy enhancers for germicides
US20050171215A1 (en) * 2004-01-30 2005-08-04 Ethicon, Inc. Germicidal compositions containing halogenated phthalaldehyes, and methods of using such compositions for disinfection or sterilization
US20050171216A1 (en) * 2004-01-30 2005-08-04 Zhu Peter C. Germicidal compositions containing phthalaldehyde mixtures and methods of using such compositions for disinfection or sterilization
US20050171121A1 (en) * 2004-01-30 2005-08-04 Zhu Peter C. Germicidal compositions containing phenylmalonaldehyde-type compounds, or mixtures of phenylmalonaldehyde-type compounds and phthalaldehydes, and methods of using such compositions for disinfection or sterilization
US6891069B1 (en) 2004-01-30 2005-05-10 Ethicon, Inc. Synthesis of 4-substituted phthalaldehyde
US7390837B2 (en) 2004-01-30 2008-06-24 Ethicon, Inc. Germicidal compositions containing phenylmalonaldehyde-type compounds, or mixtures of phenylmalonaldehyde-type compounds and phthalaldehydes, and methods of using such compositions for disinfection or sterilization
US7476767B2 (en) 2004-01-30 2009-01-13 Ethicon, Inc. Alpha-hydroxy sulfonate aldehydes, germicidal compositions containing the alpha-hydroxy sulfonate aldehydes, or mixtures of alpha-hydroxy sulfonate aldehydes and phthalaldehydes, and methods of using the compounds or compositions for disinfection or sterilization
US20070004808A1 (en) * 2005-06-29 2007-01-04 Zhu Peter C Forming germicidal aromatic dialdehydes with acetals
US7291649B2 (en) 2005-06-29 2007-11-06 Ethicon, Inc. Forming germicidal aromatic dialdehydes with acetals
WO2007078163A1 (en) * 2006-01-05 2007-07-12 Lg Chem, Ltd. Stable composition of aromatic dialdehyde and method for stabilizing aromatic dialdehyde
US20110009493A1 (en) * 2008-02-12 2011-01-13 Larry Kent Hall Broad Spectrum Disinfecting and Sterilizing Composition

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DE69908206T2 (de) 2004-03-25
EP0937395A1 (en) 1999-08-25
EP0937395B1 (en) 2003-05-28
CA2259707A1 (en) 1999-07-21
DE69908206D1 (de) 2003-07-03
ES2200467T5 (es) 2010-08-19
ES2200467T3 (es) 2004-03-01
EP0937395B2 (en) 2010-06-09
AU1318099A (en) 1999-08-12
CA2259707C (en) 2010-08-17
AU747387B2 (en) 2002-05-16
US6071972A (en) 2000-06-06
DE69908206T3 (de) 2010-12-30
JP2000001406A (ja) 2000-01-07

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